Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 20, Problem 55P
Interpretation Introduction
Interpretation:
The short segment of hyaluronic acid is to be drawn.
Concept Introduction:
Hyaluronic acid is a
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Mannose is a monosaccharide involved in the glycosylation of certain proteins.
Several genetic disorders are associated with enzymes involved in mannose
metabolism.
Monosaccharides form a new functional group when the straight chain sugar
cyclizes. What is the type of functional group formed in mannose after it
undergoes cyclization to form the furanose ring?
HO
OH
OH
0-
OH
OH
A) aldehyde
B) ketone
C) hemi-acetal
D) ether
E) ester
Part A
What are glycosides, and how can they be formed?
A glycoside is the acetal product that results from rerction of the hemiacetal -OH group of a carbohydrate with an aldehyd
O A glycoside is the acetal product that results from reaction of the hemiacetal-OH group of a carbohydrate with an alcohol.
A glycoside is the hemiacetal product that results from reaction of the acetal-OH group of a carbohydrate with an alcohol.
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In an aqueous solution, d-glucose exists in equilibrium with two six-membered ring compounds. Draw the structures of these compounds.
Chapter 20 Solutions
Organic Chemistry (8th Edition)
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Prob. 4PCh. 20.3 - Prob. 5PCh. 20.3 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - Prob. 8PCh. 20.5 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.5 - Prob. 11PCh. 20.6 - Prob. 12PCh. 20.6 - Prob. 13PCh. 20.6 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.8 - Prob. 16PCh. 20.9 - Prob. 18PCh. 20.10 - Prob. 20PCh. 20.10 - Prob. 21PCh. 20.10 - Prob. 22PCh. 20.11 - Prob. 23PCh. 20.11 - Prob. 24PCh. 20.12 - Prob. 25PCh. 20.12 - Prob. 26PCh. 20.14 - Prob. 28PCh. 20.15 - Prob. 29PCh. 20.15 - Prob. 30PCh. 20.16 - Prob. 31PCh. 20.17 - Prob. 32PCh. 20.18 - Refer to Figure 20.5 to answer the following...Ch. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 20 - Prob. 50PCh. 20 - Prob. 51PCh. 20 - Prob. 52PCh. 20 - Prob. 53PCh. 20 - Prob. 54PCh. 20 - Prob. 55PCh. 20 - Prob. 56PCh. 20 - Prob. 57PCh. 20 - Prob. 58PCh. 20 - Prob. 59PCh. 20 - Prob. 60PCh. 20 - Prob. 61PCh. 20 - A hexose is obtained when the residue of a shrub...Ch. 20 - Prob. 63PCh. 20 - Prob. 64PCh. 20 - Prob. 65PCh. 20 - Prob. 66PCh. 20 - Prob. 67PCh. 20 - Prob. 68PCh. 20 - Prob. 69PCh. 20 - Prob. 70PCh. 20 - Prob. 71PCh. 20 - Prob. 72PCh. 20 - Prob. 73P
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- 1 Hyaluronic acid acts as a lubricant in the synovial fluid of joints. In rheumatoid arthritis, inflammation breaks hyaluronic acid down to smaller molecules. Under these conditions, what happens to the lubricating power of the synovial fluid?arrow_forwardThe following molecule has a glycosidic bond that is best described as HỌ— CH2 НО HO-CH2 НО OH O OH alpha-1,4-glycosidic bond beta-1,6-glycosidic bond alpha-1,6-glycosidic bond beta-1,4-glycosidic bond OH OH OH. H2Oarrow_forwardThe following molecule has a glycosidic bond that is best described as HỌ – CH2 НО HỌ – CH2 HO OH O ОН alpha-1,4-glycosidic bond beta-1,6-glycosidic band alpha-1,6-glycosidic bond beta-1,4-glycosidic bond ОН OH OH.H2Oarrow_forward
- Which bond is not considered a glycosidic bond? Between an anomeric carbon and an alcohol oxygen. Between the oxygen of carbon 3 of ribose and a phosphate. Between an anomeric carbon and the nitrogen of acetylamine. Between the oxygen of one anomeric carbon and the carbon of another anomeric carbon.arrow_forwardArachidonic acid is a 20-carbon polyunsaturated essential fatty acid with 4 double bonds at positions omega-6, omega-9, omega-12, and omega-15. Draw the naturally occurring form of this fat.arrow_forwardAncient peoples used salicin to reduce fevers. Write an equation for the acid-catalyzed hydrolysis of the glycosidic bond of salicin. Compare the aromatic product with the structure of acetylsalicylic acid (aspirin). Use this information to develop a hypothesis explaining why ancient peoples used salicin to reduce fevers.arrow_forward
- Cellulose, the major structural material of wood and plants, consists of a chain of B-D-glucose molecules connected by B-1,4-glycosidic bonds. In comparison, the amylose component of starch consists of a-D-glucose molecules connected by a-1,4-glycosidic bonds. Identify the following structures, denoted A and B, as the structures of cellulose or amylose. A В 0 Н CH2OH H . н Н OH H Н CH₂OH 0 Н ОН Н ОН Н Н ОН О О Н Н CH₂OH -0 Н OH H Н CH₂OH 0 Н ОН Н ОН Н Н ОН OB is the structure of cellulose, while A is the structure of amylose. O A and B both represent the structure of amylose. O A is the structure of cellulose, while B is the structure of amylose. O A and B both represent the structure of cellulose. Н 0 0 H Н CH₂OH до Н ОН Н Н H OH CH₂OH 0 Н ОН Н Н Н ОН Н О Н H CH₂OH -о Н ОН Н Н ОН CH₂OH 0 H OH HA Н ОН Н H 0arrow_forwardCellulose, the major structural material of wood and plants, consists of a chain of B-D- glucose molecules connected by B-1,4-glycosidic bonds. In comparison, the amylose component of starch consists of a-D-glucose molecules connected by a-1,4-glycosidic bonds. Identify the following structures, denoted A and B, as the structures of cellulose or amylose. CH,OH CH2OH CH2OH CH2OH H. H H H H. H. OH H. H. H. ОН Н H Н но O. Н но H. OH H. ОН H. OH H OH CH2OH CH2OH H. CH2OH H. H. ОН Н ОН Н H CH2OH H H. ОН Н H. H OH H. H. H OH OH H H. H. ОН H. OH O B is the structure of cellulose, while A is the structure of amylose. O A and B both represent the structure of cellulose. O A and B both represent the structure of amylose. O Ais the structure of cellulose, while B is the structure of amylose.arrow_forwardVanillin (4-hydroxy-3-methoxybenzaldehyde), the principal component of vanilla, occurs in vanilla beans and other natural sources as a b-d-glucopyranoside. Draw a structural formula for this glycoside, showing the d-glucose unit as a chair conformation.arrow_forward
- Triacylglycerides obtained from animal fats and plant oils are typically used in the production of biodiesel. Explain the advantage of using a triacylglyceride as the starting material for biodiesel synthesis over the waxy esters found in Jojoba oil.arrow_forwardD The following disaccharide contains a(n) (blank]-glycosidic linkage. HO CH₂OH ОН Oa-1,4 OB-1,4 a-1,6 O B-1,6 0 OH Question 6 double bond ssignments/syllabus ester bond ether bond amide bond HO A glycosidic bond between two monosaccharides can also be classified as a(n) [blank). OH OH Melebi OH MacBook Proarrow_forward
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